Preppy and Proud: Tommy Bahama's Bradley O'Brien

Tommy Bahama executive Bradley O’Brien talks East Coast convention out West
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Bradley O’Brien held top roles at Sperry Top-Sider, Ralph Lauren, Lands’ End and Old Navy before joining the Tommy Bahama design and product development team last year as its executive vice president, but her fashion history started long before her impressive résumé. “My grandfather worked for Macy’s, and my dad worked at Joseph Magnin and Gucci, so I guess it was multigenerational,” she jokes. “My parents owned two women’s clothing stores in New Jersey. Calvin Klein and all these designers would come for dinner, so I was always surrounded by [fashion]. It was in my blood.”

Born and raised on the East Coast, O’Brien credits her environment with influencing her classic “preppy” style. “The Official Preppy Handbook came out during my formative years,” O’Brien says. “When I was younger, I loved Katharine [Hepburn] and Audrey Hepburn. They had that little touch of testosterone, feminine but with a tomboy edge, that I liked. I think that’s part of the whole preppy aesthetic. It’s a bit more ‘one of the boys.’”

O'Brien's preppy uniform consists of white jeans and flat sandals (which she delights in being able to wear almost year-round on the West Coast), lots of scarves and a carefully-curated bevy of bracelets stacked along her left wrist, ranging from an Hermes Chaine d'Ancre bauble (a "splurge" bought in Paris after a good year), to a cowrie shell lanyard; her son wears the matching strand. "I like to collect things," she says. "I'm so lucky I get to go to these amazing places all over the world, so I pick things up along the way."

When O’Brien isn’t jetting off to Saint-Tropez to buy prints or South America to source color palettes, she prefers being at home in Madison Park with her family and in her garden. Red Ticking, Guesthouse and City People’s Garden Store are some of her favorite local haunts for home decor.